Anionic surfactants are useful in a variety of applications. Most common among the anionic surfactants are the sulfates and sulfonates. In applications involving extremes of pH and/or high temperatures, sulfonates are preferred over sulfates due to their greater thermal and hydrolytic stability.
Sulfonates are generally prepared by the reaction of SO.sub.3 with hydrocarbon acceptors such as alkenes and arenes. Conventional sulfonate surfactants are typified by the petroleum sulfonates and alkylaryl sulfonates such as dodecylbenzene sulfonates.
Polymers containing multiple sulfonate groups are known. Typically, such polymers are prepared by the copolymerization of vinylic sulfonic acid monomers, such as 4-styrene sulfonic acid with other vinyl monomers.The relative high cost of vinylic sulfonate monomers has limited their use in surfactant applications.
In U.S. Pat. No. 4,574,061, alkoxyaryl sulfonates having up to five repeating aryl sulfonate units per molecule are disclosed. The sulfonates are represented by the general formula: ##STR1## wherein R is a C.sub.6 -C.sub.20 hydrocarbon or substituted hydrocarbon group, R' is from the group consisting of hydrogen and lower alkyl of from one to four carbon atoms, x is an integer having a value between 0 and 50 and y is an integer within the range of 1 to 5. These alkoxyaryl sulfonates are prepared by the reaction of an epihalohydrin capped alcohol or alkoxylated alcohol with phenolsulfonic acid.
U.S. Pat. No. 2,861,101 discloses polysulfonic acid polymers. The disclosed compounds are prepared by reacting polyepichlorohydrin with an alkali metal sulfite salt. The polyepichlorohydrin disclosed was polymerized using propylene glycol as the oxide acceptor or initiator. The compounds disclosed in this patent can be represented by the general formula: ##STR2## wherein n is a plural integer and X is hydrogen or a salt-forming cation.
The reaction of phenol with an epihalohydrin is disclosed in Makromol. Chem. Rapid Comm., 3, 617-622 (1982); (CA 97,145413). The disclosed reaction may be represented by the following formula: ##STR3## An additional reaction of a phenolic compound with polyepichlorohydrin is disclosed in Japanese Patent No. 73 03707 (CA 80,27723). This reaction can be represented by the following formula: ##STR4##
Surface active compounds (e.g., Na N-(1-dodecyloxy-2-hydroxy propyl)-N-methylaminoethane sulfonate) are disclosed in CA 55, 21628. These compounds are prepared from glycidyl ethers and amino sulfonates (e.g., Na methylaminoethane sulfonate or Na aminobenzene sulfonate).